The Blog

The black hole of most strategic plans

My client, Mike, is a busy entrepreneur. Whirling around like a Tasmanian devil traveling to client sites. Putting out fires. Encouraging employees. There’s barely enough time to handle strategic planning, much less the kind of “what if” planning should his airplane crash. Or car veer off the road on the way to a speaking gig.

He dragged his feet the same way people do when creating a Will. They don’t want to think about it because they’re afraid of bad juju. Like you’re asking Death to come knocking.

But as I told Mike, here’s the paradox:

When you give the “what if” part of your strategic planning some serious thought, you actually stop thinking about it.

Life insurance. A small business is often the sole or primary source of household income. Life insurance helps bridge the gap and provide funds for your family to live on for a time, until they get back on their feet.

Important business documents. An unprepared seller attracts vulture buyers eager to prey on the misfortune. You can shore up your position with: • A business operations manual • An organized customer list or database • A list of passwords to your various accounts • A folder with important legal documents, like copyright and trademark registrations, leases, or other contracts • If your business has multiple owners, a business ownership agreement, such as shareholders’ or LLC operating agreement • Your own Last Will and Testament and personal estate plan

A winding-up account. This would be a bank account that can cover at least three months of all expenses. This gives your spouse/partner—and advisors—time to get a handle on your vendors, when payments are due, and notice periods for closing out accounts.

Power of attorney. If you opened up any accounts in your own name, a properly executed Power of Attorney can allow another person to act on your behalf to wrap up your affairs. Otherwise, your heirs may have to file a probate proceeding, which can become a drawn-out and expensive process.

Letter of instruction. A letter of instruction indicating where to find documents, which items are most urgent, and who might be an interested buyer can save your heirs DAYS looking for this information. It also spares them any worry about “What would [you] have wanted?” Also give them contact information for your trusted advisors; they may have information that can speed the wrap-up process.

So as Mike started to check some of these things off his list, he felt calmer. He realized how much worry and mental energy he gave to the “what ifs” every time he stepped on a plane. Now he know his wife and four-year-old son will have support … and a strategic plan in case the “what ifs” come to pass.